7alpha-Thiospironolactone

Base Information

• Chemical Name: 7alpha-Thiospironolactone
• CAS No.: 38753-76-3
• Molecular Formula: C22H30 O3 S
• Molecular Weight: 374.544
• UNII: 4LH70U7H4Z
• DSSTox Substance ID: DTXSID20959566
• Nikkaji Number: J440.878K
• Wikipedia: 7%CE%B1-Thiospironolactone
• Wikidata: Q27260010
• ChEMBL ID: CHEMBL3544689
• Mol file: 38753-76-3.mol

Synonyms:7 alpha-thiospironolactone;deacetylspironolactone;SC 24813

Chemical Property of 7alpha-Thiospironolactone

Chemical Property:

• Boiling Point: 561.7°Cat760mmHg
• PKA: 10.18±0.60(Predicted)
• Flash Point: 457.3°C
• PSA: 82.17000
• Density: 1.22g/cm³
• LogP: 4.50240
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 374.19156599
• Heavy Atom Count: 26
• Complexity: 714

Purity/Quality:

99%, ^*data from raw suppliers

7α-ThioSpironolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CC(C3C2CCC4(C3CCC45CCC(=O)O5)C)S
• Isomeric SMILES: C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)S
• Uses: A metabolite of Spironolactone.

Technology Process of 7alpha-Thiospironolactone

There total 2 articles about 7alpha-Thiospironolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

SPIRONOLACTONE (52-01-7) → 3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + canrenone (976-71-6)

Guidance literature:

With sodium hypochlorite; octabromotetrakis(2,6-dichlorophenyl)porphyrin Fe(III)Cl; In water; acetonitrile; at 80 ℃; for 0.833333h; Microwave irradiation;

Reference yield:

SPIRONOLACTONE (52-01-7) → 15α-hydroxycanrenone (58551-67-0) + 1β-hydroxycanronene + 1α-hydroxycanrenone + 1-dehydro-15α-hydroxycanrenone + 3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + 3-(17β-hydroxy-3-oxo-1,4,6-androstadien-17α-yl)propionic acid γ-lactone (6785-74-6) + canrenone (976-71-6)

Guidance literature:

With aspergillus alliaceus; Microbiological reaction;

DOI:10.1016/j.steroids.2017.10.003

Reference yield: 77.0%

3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + methyl iodide (74-88-4) → 7-Thiomethylspirolactone (38753-77-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 0.5h; Reagent/catalyst; Solvent; Time;

DOI:10.1016/j.steroids.2012.09.005

upstream raw materials:

SPIRONOLACTONE

Downstream raw materials:

7-Thiomethylspirolactone

canrenone

3-oxo-17α-pregna-4-ene-7α-(p-methoxybenzylthia)-21,17-carbolactone

3-oxo-17α-pregna-4-ene-7α-[4-(t-butyldimethylsilyloxy)-benzylthia]-21,17-carbolactone

Refernces

• 1、 -. "EX VIVO METHODS FOR PREDICTING AND CONFIRMING IN VIVO METABOLISM OF PHARMACEUTICALLY ACTIVE COMPOUNDS". Page/Page column 36; 37; 38. . Retrieved 2015/06/25.